


Hold the Line

by watchitbuster



Category: Supernatural
Genre: Background Relationships, M/M, Meet-Cute, Minor Balthazar/Castiel (Supernatural), Minor Lisa Braeden/Dean Winchester, Miscommunication, POV Dean Winchester, Romantic Comedy, Star Trek References, When Harry Met Sally AU, Work In Progress, annoyed with each other to friends to lovers
Language: English
Status: In-Progress
Published: 2021-02-22
Updated: 2021-03-08
Packaged: 2021-03-12 12:22:08
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,392
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29634585
Author URL: https://archiveofourown.org/users/watchitbuster/pseuds/watchitbuster
Summary: Can two friends sleep together and still love each other in the morning?
Relationships: Castiel/Dean Winchester
Comments: 10
Kudos: 27





	1. Summer 1978 – University of Kansas

**Author's Note:**

> This past Valentine's day the rats discord watched _When Harry met Sally_ and since it's 2021 and cringe culture is dead, one thing led to another and, yeah. This happened. It's exactly what it says on the tin so, enjoy? Hoping to update semi regularly.
> 
> Title is from Toto’s “Hold the Line” because _Love isn’t always on time_

It’s the early hours of the morning but the summer sun is already high up in the sky. Dean stifles a yawn as he pulls into the campus parking lot. He smiles sleepily when he spots his girlfriend Cassie waving at him from the curb. Next to her stands a man, bundled up in a trench coat despite the temperature already being in the 60s at six am. He eyes the Impala suspiciously, visibly second guessing his choice of spending the next nineteen odd hours in it.

Dean shrugs before putting the car in park and stepping out. He’s the one doing the man a favour after all; if it were up to him, Dean would be more than happy to make the drive up to New York on his own.

“Hey babe,” he bends down to kiss Cassie, who flings her arms around his shoulder to deepen the kiss.

Lost in the kiss, Dean only pulls back slightly at the sound of a pointed cough from the other man. Cassie rolls her eyes and steps aside to do introductions.

“Right so Dean, this is Castiel. Dean Winchester, Castiel Novak. From my journalism class.”

Despite looking dead on his feet, hair still bed rumpled and deep bags under his eyes, Castiel is wearing a suit and tie under his trench coat. He looks like he would rather be anywhere else than here, now, about to get in a car with a perfect stranger.

Out of nowhere, Dean is struck by just how unfathomably blue Castiel’s eyes are.

“Nice to meet you.” He even sounds like he’s running on two hours of sleep and half a pack of cigarettes.

“Trunk door’s open,” Dean nods noncommittally towards the back of the car before going back to his goodbye necking session.

He is genuinely going to miss Cassie, even if both of them had decided that they weren’t going to try for long distance. They had a few months of fun, but the reason Dean was leaving Kansas in the first place was because he needed a clean start, away from anyone he knew. After Sam left for California there was nothing but a deadbeat drunkard of a father tethering him there anyway.

They’re interrupted a second time by a drawn-out honk.

Dean turns around to see Castiel in the passenger seat, the picture of perfect innocence.

“I’ll call you,” Dean promises, before leaving a final kiss on Cassie’s forehead and getting into the car.

* * *

“So Castiel huh?” Dean asks as he pulls onto the highway heading east. “Did you guys become friends ‘cause you have similar names? That’s kinda cute.”

“Please shut up.” Next to him, Castiel has lowered himself on the seat until his head is cushioned against the backrest, eyes closed. “It’s way too early for me to do small talk.”

“Okay, _Cas_.” Dean smiles. “Let’s get you some caffeine so you’re less of a cranky bastard.”

This gets him a half cracked open eye and a sleepy grimace.

They stop at a gas station so Dean can top up the Impala, while Cas buys them coffee to drink in the car. It’s the cheap stuff, but it’s warm and dark and Cas visibly perks up even just a few sips into it.

“Okay, let’s try this again,” he says, clears his throat. “Hello Dean.” His voice is still tarpit deep and gravelly, and Dean will just have to learn to live with it apparently.

“Hi sunshine, not really a morning person, are you?”

“No, I – Might also have had a late one last night.” Cas frowns into his coffee.

“Let me guess, had to say goodbye to your sweetheart?” Dean can be sympathetic, saying goodbye to Cassie was a bitch, even if they were both comfortable with a clean break.

“Something like that.”

Dean studies the man out of the corner of his eye. Cas has taken off the trench coat at some point and it’s now evident that the suit and tie wasn’t necessarily a conscious fashion decision from this morning, as much as a case of wearing the same clothes from the night before. The top two buttons of his shirt are undone and his tie hangs loosely around his neck. He looks rumpled and miserable and there goes that part of Dean, that unshakeable need to make the people around him happy.

They have nineteen hours to kill until New York and he likes a challenge.

“Okay. Why don’t you tell me the story of your life?”

Cas looks at him, head tilted.

“The story of my life isn’t even going to get us to Kansas City. I mean. Nothing’s happened to me, that’s why I’m going to New York.”

“So something can happen to you?”

“Yes.”

“Like what?”

Cas pauses.

“Not sure yet. Get into journalism school, have my own apartment, adopt a cat, fall in love. Not necessarily in that order.”

Dean can’t stop his grin, because of course he’d be stuck in a car with a hopeless romantic.

“What?” Cas narrows his eyes at him.

“Nothing. I bet you’re the kind of cheerful person who dots his _i_ ’s with little hearts.”

Cas rolls his eyes and that has no rights looking as endearing as it does.

“Sorry, I find the whole dark and brooding schtick boring as hell.”

“Fair enough.” Dean gets an idea. “Hey do you mind just,” he waves at the steering wheel and before Cas can do anything he’s diving in the footwell on the passenger side for a cassette tape.

“Jesus Christ Dean!” Cas lunges to put a hand on the steering wheel, crushing the empty styrofoam cup in his other fist. “Are you trying to kill us before we even make it out of Kansas?”

“Wanted to check if your reflexes were good enough. Ah, there we go.” He straightens back up and pushes a tape in the car’s radio. The opening notes of _Whole Lotta Love_ fill the car and Dean immediately starts beating the tempo against the steering wheel.

“Who’s this?” Cas asks, his face scrunched up in confusion.

Dean turns to look at him before Cas gestures ahead of them like he’s genuinely scared Dean will drive them off the road.

“Dude, have you been living under a rock this past decade or something?”

Cas just stares.

“Led Zeppelin? Greatest hard rock band of the 20th century?”

“There’s still about twenty years left in this century.”

“Still, _Ramble On_? _Immigrant Song_? _Black Dog_??”

“Sorry Dean, this is just not the kind of music my parents would have approved of me listening to.”

Dean snorts. “And you do everything your parents approve of, huh.”

“Yes,” and Cas’s voice is glacial. “Which is why I’m hitching a ride to the other side of the country with a complete stranger.” His words are dripping with harsh sarcasm and it hits Dean that maybe he’s not the only one who’s trying to leave a whole lot of baggage behind and start fresh somewhere new.

They’re both silent as _Whole Lotta Love_ gives way to _What Is and Should Never Be_.

It’s Cas who mercifully breaks the silence next.

“What about you, what are you going to do in New York?”

“There’s this uh, family friend. More like family period. Sort of uncle kind of guy. Anyway, he’s got this garage and asked me to come over and give him a hand with running things.” Dean shrugs. “Haven’t really got anything keeping me here so I said yes.”

“You don’t have any family here in Lawrence?”

“Little brother graduated high school and fucked off to California because he’s a baby genius. Stanford, you know.” And dammit it does make him proud to say out loud, even if it makes his stomach churn with how much he misses the kid. He chews the inside of his mouth for a beat before quickly doing the rest of the family rundown. “Mom died when I was four and Sam a six-months old baby. Dad is. Not really in the picture anymore.”

His grip tightens on the steering wheel, against the pity or concern or whatever Cas is going to throw at him, but to his relief, Cas only nods.

“Let me know when you want me to take over.”

“With… family stories…?”

Cas rolls his eyes, but there’s a faint smile on his lips. Dean is sure that’s the first time he’s seen him smile so far and some part of him irrationally wants to see more of it.

“With driving, Dean.”

“Ah yeah, I don’t think that’s gonna happen, sorry.”

“Dean. You can’t be suggesting you’ll drive _the entire nineteen hours of this trip_.”

Dean is silent in response.

“Oh okay, so you really are bent on killing the both of us,” Cas deadpans.

* * *

Somewhere in Illinois, they stop for a late lunch.

“So wait. He literally has to mate or he dies?”

“Yes.” Dean rolls his eyes before opening the car door and stepping out.

“But you said,” Cas follows him, standing close so he can finish making his point. “You said he thought he had _killed_ Kirk and that was enough for him to lose all desire for the woman.”

“ _Yes_.”

They make it to the door of the diner before Cas speaks again.

“So the fight was a sex metaphor?” Cas gestures to the host as they step inside. “Table for two please.”

Dean freezes just behind him.

“I- He- It was not a _sex_ metaphor,” his voice is so much louder than he thought. He feels every eye in the diner on him. “It was _not_ ,” he whispers loudly again.

They sit across from each other and Cas looks at him, head tilted and half a smile.

“Dean.” He starts listing on his fingers. “Spock must have sex or he dies. Kirk and Spock fight. Afterwards, Spock does not need to have sex anymore. Ergo…”

“Please shut up.”

Dean is saved from the mortifying ordeal of listening to someone – to _Castiel_ – discuss Kirk and Spock’s sexual relationship by the waitress coming to take their orders.

“Hiya boys, what can I get you?”

“I’ll have a cheeseburger and fries, thanks.”

When the waitress turns to Cas, all traces of humour are gone from his face.

“I’ll have the chef’s salad with the oil and the vinegar on the side and the apple pie a la mode.”

The waitress starts writing but Cas is not finished.

“But I’d like the pie heated, and I don’t want the ice cream on top, I want it on the side. And I’d like strawberry instead of vanilla if you have it. If not, no ice cream, just whipped cream, but only if it’s real. If it’s out of a can, then nothing.”

The waitress stares at him. “Not even the pie?”

“No, just the pie,” Cas replies primly. “But then, not heated.”

The waitress leaves in disbelief and Cas looks Dean in the eye, daring him to say anything.

Dean shakes his head but can’t help smiling at Cas.

“Nothing.” Before Cas can say anything more, Dean starts up again. “Okay so anyway that was season two episode one, _Amok Time_. The second episode in season two is called _Who Mourns for Adonais?_ and it starts with this weird green beam, okay? That’s shaped like this bigass hand and it grabs the Enterprise and stops it from moving so Kirk is like _what the fuck_ right?”

“Right.”

* * *

When the bill comes, Dean finds himself lost in the little crease that forms between Cas’s eyebrows as he focuses on calculating the tip. He had hoped to not be so obvious, but when Cas looks up, he catches Dean staring.

Cas rubs at the corner of his mouth in confusion.

“What, do I have something …?”

Before Dean can even stop to consider the implications of what he’s about to say, he blurts out, “You’re a very attractive person.”

Cas shifts a little in his seat and the colour starts to rise in his cheeks and Dean is not supposed to look, he is _not_ , for _so_ many different reasons, but hell if that isn’t just a great look on the man.

“Oh, um.” Cas clears his throat and there’s a hint of a question in his next words. “Thank you?”

“Just sayin’, Cassie never mentioned you being so attractive.”

Cas’s lips jerk up to one side. “Well maybe she doesn’t think I’m attractive.”

“Not possible dude. You’re like, empirically attractive or some shit.”

“Dean.”

“Yeah.”

“Cassie is a friend of mine.”

“Yeah so.”

“A _female_ friend of mine.”

Dean frowns. Last time he checked that seemed to have been the case.

“Not following.” He picks at the last couple of fries in his plate just to have something to do with his hands.

Cas sighs with his entire body. He pushes at his rolled-up sleeves – because he’s not wearing his suit jacket anymore and his lean forearms are just there, for everyone to see, and it’s not really fair to judge Dean for looking. He starts to settle his elbows on the sticky diner table, but squints at it before deciding against it.

Finally, he says, “It would not make a difference if she found me attractive since I am very much a homosexual.”

The fries freeze midway between the plate and Dean’s mouth.

 _This would be the window_ , his brain suggests, the perfect moment handed to him on a plate. There would be no judgment in Cas’s face if Dean were to say here, now, under the sharp fluorescent lights of this dingy diner, that Dean Winchester is also attracted to men.

He’s never said it out loud is the thing. Never really had a chance to act on it anyway so what would have been the point. But here and now, it would be so simple. A passing remark. An appendix on the story of his life. _By the way, I think dudes_ and _chicks are just groovy_. He could just _say. It._

Too bad Dean Winchester is a coward.

“What,” Dean shoves the fries in his mouth and forces a chipmunk smile. “Can’t a man compliment another man without it being a come-on?”

Cas tenses a bit, almost looks… disappointed? He ducks his head slightly before he tersely says, “No, of course you’re right. Sorry, didn’t mean to make you uncomfortable.”

Right, humour as deflection, not always the best course of action. Dean rushes to correct because he might be a coward, but he’s not a complete piece of shit. Yet.

“Shit no dude, you’re good. That was a shitty joke. Sorry.”

Cas still looks at him quizzically, not quite sure what to make of Dean. Raging homophobe or just awkward asshole?

“Look,” Dean raises his hands. “I take it back okay? I take it all back. You’re not attractive, in fact you’re an ugly son of a bitch.”

Finally, Cas smiles at him and okay, yes Dean is definitely lying out of his ass calling this man ugly.

“Too late.”

“What...?”

“You can’t take it back, it’s already out there.” And Cas has the audacity to wink at him. “You think I’m attractive.”

Dean rolls his eyes and pulls a few notes out of his wallet to drop on the table between them. The sooner they get back in the car, the sooner he can stop having to look at Cas’s distractingly blue eyes straight on.

“Let’s just get the show back on the road, shall we?”

* * *

“So who’s the boyfriend you had to say goodbye to last night? Anyone I know?”

It’s only when they’re across the next state line that Dean feels comfortable enough to bring the subject back up. Since the diner they had mostly shared a companionable enough silence. Cas had insisted he wanted to take a turn driving and once the vast flatness of Ohio stretched before them, Dean had agreed. Begrudgingly.

Cas stares ahead resolutely and a muscle jumps in his jaw.

“No, I really don’t think so.”

Dean studies him for a second longer before pushing for more.

“Was it that bad of a breakup?”

“I am not talking about it.”

“Fine! I don’t need to know.”

They’re silent once more and Dean starts rifling through the pile of cassette tapes in the glove compartment for something to fill the silence.

“If you must know,” Cas suddenly says. He’s not looking at Dean and his grip on the steering wheel is white knuckled. “It’s because he was very jealous and I had these Days of the Week underpants.”

Dean stares at him, blankly trying to piece the two thoughts together.

“He… you what?”

“They had the days of the week on them, I thought they were kind of funny,” Cas huffs. “And one day he said to me ‘you never wear Sunday’. He got all suspicious. Where was Sunday? Where had I left Sunday? And I told him that they don’t make Sunday, but he didn’t believe me.”

Dean is still staring and the only thing that comes out of his mouth is, “Why don’t they make Sunday?”

Cas turns in his seat so he can briefly look at Dean, a blank expression layered across his blue eyes.

“Because of the Lord, Dean.”

The first sound Dean makes is like air slowly leaving a balloon. Then something stronger starts deep in his chest, bubbling to the surface like overboiled chili and filling him up until all he can do is let it out, loud and violent. He’s laughing so hard, he’s fleetingly grateful he’s not driving right now or he probably would have swerved into oncoming traffic.

“Fuck, that was funny Cas,” he manages to say in between gasping breaths. Cas looks a bit like the cat who got the cream, a twinkle of amusement in his eyes even as he’s back to staring at the road ahead. “And that’s what broke you up?”

“Yes. Plus he was my TA so you know. Whole lot of bad decisions all around.”

Dean whistles. “Way to stick it to your parents.”

There is silence and Dean feels content to look out of his window. _This is nice_ , he realises. Joking and talking to Cas, sharing a space without the need of posturing, without assumptions. The potential of a new life in New York comes with the freedom to form new relationships, to be someone different, and most importantly with time to properly come to grips with new parts of himself that he had felt the need to hide for so long. Yes, Cas’s friendship could be a stepping stone to something new.

Hey maybe at some point he might even be able to come out to the guy! Just for the hell of it.

When Cas next speaks, it’s to throw a wrench in exactly this train of thought.

“You realise of course that we can never be ‘friends’?” and Cas puts a hand up and honest to god mimes air quotations on each side of his carefully enunciated last word. Dean’s face contorts into two consequent but diametrical opposite expressions. He wants to smile but his brow furrows in confusion.

“What do you mean?”

“What I’m saying – and please do not take this the wrong way – is that a straight man and a gay man can never be just friends.”

Ah. Yes. Right. Cas would have no way of knowing about Dean’s bisexual panic.

Dean bristles anyway.

“Why not?”

“The sex part always gets in the way.”

“What sex part?”

“The men having sex with other men part,” Cas deadpans.

Dean’s brain goes offline momentarily.

“Oh.”

“Look, I know how this goes. Straight men are obsessed with the idea of protecting their masculinity and to do so they overcompensate to a truly obnoxious degree.” A beat, before Cas’s voice softens. “It’s nothing against you personally, I just really don’t think we would have anything in common.”

“Well,” Dean goes back to looking outside his window, walls back up. “I guess we’re not going to be friends.”

And why would Cas want to be friends with him anyway. He’s not a closeted mess for starters. Has a college education for seconds, while Dean only hung around campus to hook up with co-eds. Cas is right, they really don’t have anything in common.

“I guess not.”

“Too bad,” Dean shrugs. “You were the only person my age I knew in New York.”

* * *

Dean insists on taking over driving when they’re just outside of Pittsburgh and there’s a new determination in the press of his foot on the gas pedal. The miles fly under them and they talk very little for the last stretch of the trip.

Dawn is still an hour away from breaking by the time they cross the Hudson.

“Well,” Dean says as he pulls up to Washington Square. “This has been interesting.”

He turns to look at Cas, who stretches lazily before he starts gathering his stuff.

“Sure was. Thanks for the ride.”

“Don’t mention it.”

The two of them look at each other and damn if those aren’t just the most remarkable eyes Dean has ever seen. He does his best to fully commit them to memory.

Cas holds out his hand.

“Have a nice life Dean.”

Before Dean can say anything more than, “You too.” Cas has pulled away and is opening his door.

The cold predawn air shocks Dean to his core and he stares as Castiel puts his trench coat back on. He walks towards the back of the car and Dean hears him popping the trunk open briefly. When he’s back in Dean’s line of vision, he’s shouldering a bag and holding onto a tattered briefcase. With one last wave in his direction, Castiel starts walking away and before long, Dean loses him in the early morning rush of people on their way to work.


	2. Winter 1983 – La Guardia Airport

**Notes for the Chapter:**

> yes it's the 80s, yes gay marriage is legal, suck on that reagan

Through the fog and the roaring sound in his ears, Dean hears the intercom announce that the boarding for his flight has started. He can’t physically postpone it any longer, not if he wants to risk missing the flight entirely. He considers the possibility one last time. Leave now and get back in his car, his beautiful, reliable,  _ grounded _ Baby, which isn’t going to hurl him across the sky with a vengeance.

Instead, he thinks of Sam, of the puppy eyes he could audibly hear over the phone when he suggested Dean fly over for the holidays so he could meet Sam’s new girlfriend. He can do this for Sammy. He can get on a flying death trap for his brother, he  _ can _ do it. He takes an unsteady breath before getting up and shouldering his duffle bag.

He’s walking with a purpose now but out of the corner of his eye he recognises a familiar face. There’s two men sharing slow kisses, clearly saying goodbye, and he can swear the taller one with the sandy hair used to live in the building a block down from Bobby’s garage. He’s pretty sure he fixed his car a few times, a 1976 Pontiac Astre.

He stops and takes a few steps back to double check, standing closer than it would probably be considered polite. Yep, definitely Balthazar.

The first one to notice him is the shorter guy and he frowns at him in confusion, before breaking apart. Before they can tell him to piss off though, Dean puts on his most charming smile.

“Balthazar, I thought that was you! Dean, Dean Winchester?”

The taller man – Balthazar – smiles in recognition and holds his hand out to shake.

“Dean! Christ, but it’s been an age. How are you?”

Dean shakes it.

“Fine, fine. How are you, still with the DA’s office?”

Balthazar’s smile is almost blinding, the sign of someone whose career is clearly rocketing sky high. Dean lets go of his hand, suddenly wondering if he managed to get all the grease out from under his nails. He shoves both hands in his pockets instead.

“Switched over to the other side. How about you? How’s the garage?”

“All good, Bobby is thinking of opening a second shop sometime in the new year, so yeah. Things are good.”

The other man fidgets beside Balthazar, somehow trying to make himself look smaller, hiding behind Balthazar’s shoulder, and Dean’s eyes flick to him absentmindedly. He almost does a double take when he recognises the man. It would have been impossible for Dean to forget those eyes, even five years after their road trip.

Balthazar remembers himself and affectionately reaches to hold the other man’s hand.

“Oh how impossibly rude of me. This is Castiel Novak. Darling, this is Dean Winchester. Used to service my car when I lived down on the East Side.”

Castiel nods, looking anywhere but towards Dean. Got it, not keen to reminisce on college days. Or maybe he just doesn’t remember Dean. After all, he had made it very clear that there was no way for the two of them to be friends. Still, Dean knows how to be civil at least.

“Hi,” he smiles.

Before things can get any more awkward than they already are, he hooks his thumb over his shoulder, pointing towards the departure terminal, and makes his escape. After all the inevitability of his demise is still looming large in the shape of an American Airlines metal death tube.

Somehow Dean makes it to his seat, although he has no memory of walking up to it. He sits heavily and puts his head between his knees to catch his breath. The woman to his left eyes him briefly before asking him if he’s okay.

Dean doesn’t really have an answer, but the woman’s voice is soothing as she talks him through the details of her trip – a visit to see her newborn granddaughter – and slowly he can feel the white noise receding. When she offers him a stick of gum, he only hesitates for half a second before he grabs it thankfully.

The plane takes off and Dean’s grip on his armrest is painful. He is seriously questioning every single decision he ever made that brought him here to this moment. The woman next to him is still talking, has moved now to describing the baby blanket she knitted over the past few months.

He tries to focus on the gentle voice, on the back of the seat in front of him, on anything that is not the reality of being suspended thousands of miles in the sky.

He seems to be able to breathe a bit better by the time the plane levels and the cabin crew starts wheeling the snack cart along the aisle.

“Do you have Bloody Mary mix?”

Well, that is certainly the last voice Dean had expected to hear.

He cranes his neck to look between the seats in front of him and there’s Castiel’s profile, seriously explaining to the flight attendant just how he wants his drink. 

“No, here’s what I would like you to do: regular tomato juice, not too much ice, fill it up about three quarters, and then add a splash – just a splash – of the Bloody Mary mix. And a little piece of lime if you please, but on the side.”

Dean can barely contain a shit eating grin. He pops his folded arms on top of the headrest and leans his chin on them to look down at Castiel.

“Haven’t changed much since the University of Kansas, huh.”

“Hello Dean,” Castiel says, without looking at him.

“Oh, so you do remember me.”

“Hard to forget the longest night of my life.”

“Didn’t know I made such a lasting impression,” Dean winks down at him.

The man sitting next to Castiel is listening in with a slightly amused tilt to his lips. Castiel catches sight of it and immediately hastens to explain.

“We drove from Kansas to New York the day after graduation.”

“Would you two like to sit together?” the man offers.

“Yes, absolutely,” answers Dean just as Castiel starts to object.

There’s a bit of shuffling as Dean exchanges seats with the man.

“Hi Cas.” Dean can’t stop smiling for some reason and suddenly the possibility of plummeting to his death has become the furthest thing from his mind.

Cas rolls his eyes and pointedly goes back to reading his book.

Dean studies him. Cas looks much more put together than he did during their interminable road trip. He’s wearing a freshly pressed suit, his cufflinks gleaming in the harsh overhead light. His hair is somewhat tamed, even though there’s little wisps of it curling obstinately at his nape. He’s clean shaven and well rested and well, no way around it, still as devastatingly handsome as he was five years ago.

“Did you look this good at KU?”

“No,” Cas says but the tip of his ears start turning red.

Dean bites back another smile. He seems to be physically unable to stop needling Cas.

“So you and Balthazar, huh.”

“Yes.” Cas on the other hand, seems intent on only giving him monosyllabic replies.

“Good, good, how long have you been together, three weeks?”

This seems to get Cas’s attention and he tilts his head to look at Dean with narrowed eyes.

“A month. How did you–?”

“You have that lovey dovey  _ no you say goodbye first _ new relationship air around you, but he also drove you to the airport so it must be sort of serious. Do you think you’re gonna marry him?”

Cas bristles a bit.

“We’re both very busy with our careers, marriage is not a priority right now.”

“Right. You were gonna be a journalist.” Dean suddenly remembers something else. “And adopt a cat! You ever got around to that?”

“I do have a semi regular column in the New York Times,” Cas answers. “Balthazar is unfortunately extremely allergic to cat fur.”

“Hm too bad. You almost got bingo there.”

Cas studies him for a moment.

“What about you, Dean?”

“Well, you heard what I told Balthazar, I’m still just your friendly neighbourhood mechanic.” He pulls up his left hand. “I did get hitched though.”

Cas’s eyes widen slightly.

“You? You’ve got married.”

“Why, is that so hard to believe?”

“No of course,” Cas smiles. “Who is she?

“Lisa Braeden, she’s an aerobics instructor and she’s awesome.”

They have only been married just over a year, but the magic still hasn’t worn off. Lisa makes him laugh and loves his cooking and it’s just damn nice to have someone to come home to at the end of the day.

“How come she’s not with you right now?”

“We were supposed to but y’know, family stuff, her sister is going through a divorce.” Dean shrugs as if it’s no big deal, even though he would have given anything to be able to hold her hand right now. “I’m going to be back before New Year’s anyway.”

As soon as the words leave his lips, the entire plane lurches, sending Dean’s stomach on a trip in the direction of his feet.

“Holy  _ shit _ .” He clenches his eyes shut.

There’s that roaring rushing noise in his ears again. He feels chills going up and down his spine, just as he feels beads of sweat starting to form at his temples.

“You okay?” Cas’s voice is laced with concern.

“Really,  _ really _ do not like flying,” he mumbles through clenched teeth.

Cas is silent next to him. Then, there’s gentle fingers plucking his hand from the death grip it holds on the armrest.

“Breathe with me Dean, focus on my voice.”

Dean follows along with Cas’s breaths, in and out. In and out. Slowly sensation starts to come back to his fingers and he feels grounded in the warmth of Cas’s hand in his.

He blinks slowly and lets out a long shaky breath. He focuses his gaze on the leather of the seat in front of him. There’s a small rip where he can see a bit of the stuffing poking out.

“Would you like me to call a flight attendant?”

Dean shakes his head minutely.

“No I’m, I’m good.”

Cas makes to remove his hand but Dean tightens his grip.

“Would you mind… just, just a little while longer,” Dean says, still not looking at Cas.

“Of course. Would it help if I kept talking?”

Dean nods and Cas starts talking about a piece he’s working on, about the changes in the neighbourhood he lives in and the impact they had on lower income families. Dean doesn’t follow everything, but it’s enough to focus on the low rumble of Cas’s voice as he feels his heart slowing down its harried pace.

He doesn’t quite notice falling asleep, but when he blinks next, they’re about to start descent into Oakland. His hand is still grasped loosely in Cas’s.

Cas lowers the book he’d been reading one-handed and smiles at him softly.

“Hey.”

“Hey,” Dean grumbles. “Can’t believe I fell asleep, I’m so sorry.”

“Don’t be, you looked like you needed the nap.”

“Heh,” Dean chuckles incredulously. “I slept almost the entire six hours.”

Cas is still smiling at him and it’s somewhat contagious, pulling an answering smile out of Dean.

Dean frees his hand and goes to stretch both arms above his head. He doesn’t notice the small disappointed crinkle between Cas’s eyebrows when he goes to lay both hands in his lap afterwards.

Landing is a bit bumpy and Dean’s heart jostles in his chest painfully, but there’s the knowledge that they have made it this far and he gets to see Sam soon, which is enough to keep his breathing even.

He and Cas gather their things and step out of the plane together, walking side by side easily.

“So, would you like to have dinner sometime?” Cas asks, quite out of the blue.

Dean gives him a look. “I thought you said gay men and straight men couldn’t be friends.”

“Well—”

But Dean doesn’t hear the rest of the sentence as, standing a full head above everyone around him, he sees his big dork of a little brother waiting just outside the arrival gate.

“Sammy!” He bellows.

Sam’s face lights up when he spots Dean and he’s ready to pull him into a crushing hug by the time Dean reaches him.

“I thought I told you I was gonna catch a cab to your place, you didn’t have to come pick me up.”

“No I know, but I also know you get nervous flying.”

Dean’s chest tightens and suddenly the six hours ordeal feels entirely worth it.

Before he can say anything else there’s a gentle tug on his elbow and he turns to face Cas. He’s hovering behind Dean, a small smile on his face.

“I will leave you to it, then.”

“Oh yeah, uh, thanks again for—”

“Don’t mention it. See you around Dean.”

“Yeah, see ya.”

They shake hands and Dean watches Cas walk away, feeling an odd sense of deja-vu. His fingers feel strangely empty.

He turns to Sam, who is looking at Dean with a question in his wide eyes.

“Um, who was that?”

“That was Cas- Castiel,” Dean says simply.

Recognition flits over Sam’s face.

“Wait, Castiel? KU road trip Castiel?”

“Yep.” Dean frowns. “We seem to keep bumping into each other.”


	3. Fall 1988 – Shakespeare & Co

Lying on Charlie’s lumpy couch, Dean starts to think the whole marriage thing is really not all it’s cracked up to be. He finds patterns to follow in the cracks in the ceiling as he wills his body to fall asleep. It’s a hard thing to do when you have just found out your wife has been having an affair for the past three months.

_ I don’t think I ever loved you _ , Lisa had said, so matter of fact it had stolen his breath.

He pushes up on his elbow to punch the pillow under his head before settling back down on his side.

He’s thankful that Charlie was willing to take him in while he looks for a new apartment. The thought of being in the same rooms where he and Lisa had slept together, where he had cooked dinner for her, where they had been a  _ family _ – a minute longer makes bile rise in his throat.

How are you supposed to start over after six years of marriage?

The first few days, Charlie gives him a wide berth, simply checking in on him around meal times but mostly leaving him to mope. She doesn’t bring up Lisa or the fact that most of Dean’s stuff is still at his – their –  _ her _ place. Unlike Sam, Charlie doesn’t seem pressed about the mountain of legal paperwork that seems intent to swallow Dean whole. Bobby is gruffly sympathetic, offering to cover his shifts at the garage for as long as Dean needs.

Dean wallows in self-pity during the day and in the evenings, he and Charlie eat pizza and watch old Star Trek reruns. As far as coping mechanisms go, he knows he could be doing much worse.

The days stretch under him and it’s hard to tell one from the next. Two weeks into it and Sam finally snaps at him over the phone. He threatens to fly across the country so he can shake some sense into Dean. It feels wrong, Dean should not be the brother who is taken care of, he should be the one who  _ takes care of _ . Some small selfish part of Dean still wants to let him.

In the end, he gruffly agrees to fax Sam the paperwork that needs looking at and, before he can second guess himself, leaves Charlie’s apartment for the first time in days.

It’s a brisk September afternoon and with no actual destination in mind, Dean wanders the streets of Manhattan. The effort of putting one foot in front of the other takes up most of his cognitive functions, but there’s still plenty of room for his brain to dedicate to the way Lisa’s hair would fall out of her messy ponytail at the end of the day.

He doesn’t really notice walking into Shakespeare & Co, of all places.

It’s quiet in the bookshop, peaceful, and Dean’s brain numbs pleasantly. Briefly, he thinks that he should get something for Charlie, something that says: “Thank You For Putting Up With My Bullshit”.

He meanders among the shelves, tilting his head this way and that to read the titles. When he reaches the Self-Help section, his brain helpfully points out all the healthy living books Lisa used to own. He’s just about ready to turn tail and flee, when he spots someone he had not been thinking of in five solid years.

Castiel Novak is standing behind a table piled high with bestsellers sporting titles such as “How to Ask for Better Orgasms”. He’s squinting at a book in his hand while a shorter woman with long dark hair points at something on the back of it. Dean studies him from across the room.

Castiel looks different. He’s not wearing a suit, for starters. Instead, he’s wearing a deep burgundy cable knit sweater and jeans. The jeans are what really throw Dean the most. He looks  _ good _ in jeans. Now that’s a thought which came out of absolutely nowhere.

The woman glances up just in time to catch him staring and, panicked, Dean hides his face in the first book he can grab.

He can hear the two of them murmuring to each other, definitely judging the creep in Personal Growth who’s staring at them from behind a book about erectile dysfunction. When Dean dares looking up, they’re both looking at him.  _ Busted _ , he thinks.

With a full body sigh, he approaches the pair, keeping the bestsellers table safely between them.

“Hi Cas,” Dean offers a weak smile. “Thought I recognised you.”

“Hello Dean,” Cas replies. His eyes are on Dean now and oh yeah, that’s right. He had almost completely forgotten the whole otherworldly blue eyes thing.

“This is M—” Cas starts, and as he and Dean turn to look, the woman is already halfway down the stairs towards the exit. She waves at them with a cheeky smile.

“ _ Was _ Meg,” Cas finishes with an exaggerated roll of his eyes.

Dean can’t help but smile more fully now.

“So how’ve you been? How’s Balthazar?”

Cas looks down at the books between them, his eyebrows pinched together even as he answers in an even, almost bored voice.

“Fine, I hear he’s doing fine.”

“You guys are not together anymore?” Dean frowns.

“Nope,” Cas shakes his head. “Just broke up not two weeks ago.”

“Hey I’m sorry man, that sucks.”

Cas waves a hand, looks back up to meet Dean’s eyes.

“What about you? How’s married life?”

It’s Dean’s turn to sheepishly avoid Castiel’s eyes. He feels his stiff shoulders bunch up to meet his ears.

“Not great,” he admits to the table. “The opposite of great actually. We’re getting divorced.”

“Dean, I’m so sorry to hear that.”

There’s a small awkward pause, before Cas walks around the table to stand closer to Dean.

“I think we should go take a walk and ‘hash things out’.”

Cas brings up his fingers to mime air quotes and Dean can’t help snorting out a laugh. There’s something familiar about the gesture and unbidden, a fleeting ten year old memory muscles its way to the front of Dean’s mind. Cas’s smiling profile bathed in the occasional street light as he carefully drives Baby along a solitary interstate highway in the middle of the night.

They walk out of the bookstore and head towards Central Park. The leaves are just starting to turn, dark reds mixed with bright yellows and the occasional solitary greens. They fall in step easily and slowly catch each other up on the past five years. Dean talks about Lisa’s affair, Cas talks about wanting to start a family and having to break up with Balthazar when he had admitted that wasn’t something he would ever want.

“We used to joke that we were so lucky not to be married because we could just, I don’t know, be spontaneous.” Cas says wistfully. “Hop on a flight to Rome on a whim or, or… have sex on the kitchen floor.”

“But?”

“Thing is,” Cas sighs. “We never did any of those things. For one, our kitchen floor was this cold hard ceramic tile.”

Dean laughs and he can see an answering smile pull at Cas’s lips.

“We just had to face the reality that we wanted different things and we were only growing further and further apart because of it.” Cas shrugs. “So we ended it.”

“Man, you make it sound so easy,” Dean mumbles.

He feels Cas’s stare on him like a physical weight. When next he speaks, Cas’s voice is softer.

“I think I owe you a long overdue apology, Dean.”

Dean stops in his tracks, turning to look at Cas quizzically. Cas stops too.

“When we first met I was, well I was an ass.”

Dean starts to open his mouth to say something, not sure what yet, but Cas holds up a hand silencing him.

“I was twenty-one and fresh out of college, and damn if I didn’t think I was better than everyone else around me. I saw your car, heard your music, and thought you were the last person I would ever find myself having anything in common with. So I didn’t even try and just gave you that ridiculous ‘we can’t be friends because I’m gay and you’re straight’ speech.”

Cas looks genuinely pained, a hand goes up in his hair, ruffling it.

“Funny thing about that,” Dean says with a small smile. He starts walking again and he hears Cas following him after a beat. “I’m not straight. I’m bi.”

Now, it’s not the first time he has said the word out loud. He told Charlie, obviously, and Sam. Lisa knew. Heck, even Bobby knows. Nevertheless, it still makes his stomach do a little somersault every time.

“Even so,” Dean hears Cas say next to him. His voice is tentative. “I would like it very much if we could start over. Have dinner sometime.”

“Are we becoming friends now?”

“I suppose we are.”

Dean hums and they keep walking in companionable silence. The late afternoon sun is low in the sky and a brisk breeze makes a bunch of leaves dance around their feet.

**Author's Note:**

> Find me on tumblr @ [watchitbuster](https://watchitbuster.tumblr.com/)


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